RT info:eu-repo/semantics/article
T1 Regioselective synthesis of elusive 4,9-Dihydro-1H-Carbazoles by gold-catalyzed cycloisomerization of 3-Allenylmethylindoles
A1 Álvarez Manuel, Estela
A1 García García, Patricia
A1 Fernández Rodríguez, Manuel A.
A1 Sanz Díez, Roberto
K1 Química orgánica
K1 Chemistry, Organic
AB A general and efficient synthesis of 4,9-dihydro-1H-carbazoles from 3-allenylmethylindoles is reported. Theprocess, catalyzed by a cationic gold(I) complex, involves aformal C2−H bond activation of the indole unit by reactionwith the allene. The nature of the substituents at the allylic andterminal positions of the allene moiety has a crucial effect onthe regioselectivity of the cyclization, which is also influenced by the catalyst and the solvent employed. Moreover, some evidenceof the contribution of different reaction routes is provided, which led us to propose a plausible multipathway mechanismconsistent with all of the results described.
PB American Chemical Society
SN 0022-3263
YR 2013
FD 2013-09
LK http://hdl.handle.net/10259/3914
UL http://hdl.handle.net/10259/3914
LA eng
NO MICINN and FEDER (CTQ2010-15358 and CTQ2009-09949/BQU) for financial support. E.A. thanks MEC for an FPU predoctoral fellowship. P.G.-G. and M.A.F.-R. thank MICINN for "Juan de la Cierva" and "Ramon y Cajal" contracts
DS Repositorio Institucional de la Universidad de Burgos
RD 25-abr-2024